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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Asymmetric synthesis of beta-hydroxy sulfides controlled by remote sulfoxides
Yolanda Arroyo1, J Félix Rodríguez, Mercedes Santos
1Departamento de Química OrgAnica (ETSII), Universidad de Valladolid, Paseo del Cauce s/n, 47011 Valladolid, Spain.
Abstract:
Reactions of (S)-alpha-(methylthio)-2-(p-tolylsulfinyl)benzyl carbanion with different carbonyl compounds proceeds with complete control of the configuration at the benzylic position. Aldehydes yield easily separable mixtures of beta-hydroxy sulfides, epimers at the hydroxylic carbon, where the stereoselectivity depends on steric factors (from 20% to >98% de).
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